Air Mater

Skipper is a gray plane who lives in Propwash Junction, a whole town full of airplanes. He runs Skipper's Flight School with his assistant Sparky, and he teaches Mater how to fly in Air Mater. Skipper learns that he can really teach anyone how to fly, guaranteed. He watches as Mater flies in the sky. Later, he and Sparky attend the air show, in which Mater was recruited as a Falcon Hawk. Sparky pointed out Skipper as Mater's mentor to Mia and Tia, impressing them.

Planes

A reclusive old Navy Corsair, Skipper was an ace flier and top instructor of the esteemed Jolly Wrenches squadron until an incident during a combat mission took him off the front lines and left him grounded for life. These days, Skipper keeps to himself, but his quiet existence is turned upside down when an ambitious and persistent Dusty solicits Skipper’s aerial expertise—and gets a few life lessons in the process. But Skipper—who’s never really come to terms with his past—finds that he has a few things to learn, too, and while coaching Dusty to fly faster and smarter, the teacher becomes the student.[1]

Skipper appears to be a little judgmental in Planes, as he hesitated to teach Dusty how to fly well at first. After Dusty passed qualifying however, Skipper then realized he had been a little harsh and agreed to help Dusty and his friends.

Planes: Fire & Rescue

According to an interview with Bobs Gannaway and Ferrell Barron on Planes: Fire & Rescue,[2] Skipper is scheduled to appear. However, it is unknown if Stacy Keach will return. Skipper will be more friendly to Dusty and does more flight exercises with him.

Trivia

Skipper's make (F4U Corsair) and Skull and Crossed Wrenches insignia on his engine cowling are clearly based upon the World War II US Navy Figher Squadron VF-17 ("The Jolly Rogers"). Skipper even has "VF-17" stenciled on his rear fuselage. In the photo, you can compare Skipper with "Big Hog", the Corsair flown by Cdr Tom Blackburn, CO of VF-17.

In the Japanese trailer of Planes, Skipper was voiced by Takaya Hashi (土師孝也), but Tarō Ishida (石田太郎), the Japanese actor of Skipper, passed away from a heart attack on September 21, 2013, while Japan was producing Planes in Japanese.